How can you not be a bit envious of Simon Rich? A former editor of the Harvard Lampoon, he was Saturday Night Live's second youngest ever scriptwriter, has already written two novels – one of which, 2010's Elliot Allagash, reads like a posthumous hit John Hughes film waiting to happen – and now, at 28, is unleashing his third collection of (New Yorker-approved) humour pieces. It would be almost a relief to find that The Last Girlfriend on Earth was another of those American humour collections by a writer (eg Sloane Crosley) falling short of their hype as an heir to David Sedaris and James Thurber, just to be reassured that Rich wasn't good at everything. As it happens, it's brilliant: a kind of modern version of Woody Allen's Without Feathers for anyone who's been in love.

The Last Girlfriend on Earth begins with the story of a man's coming of age, told through the autobiography of his lone condom, which finds out manifold horrifying things about itself by talking to the other items that live in the man's wallet ("I am too embarrassed to admit the truth, which is that I thought I was a balloon"). Only a couple of times within the next 29 pieces does Rich hit a note that's not either topsy-turvy imaginative, riotously funny or hugely insightful. In Wishes – which says a lot about men and porn without really mentioning porn – a woman is aghast to find the depraved ways her boyfriend has used 50 wishes granted by a genie. "Why do you think there is no world peace?" the genie asks her. "Because no man ever wishes for it." By contrast, Future uses a time machine joke to tell the touching tale of a necessary break-up. Beneath the clear ambition to make people laugh, there's another book lurking here: a guide to the idiocy and sensitivity of men that could be more valuable to the opposite sex than a million "How To Please Him" women's mag articles. Rich has a wisdom about male-female interaction that most have to wait far, far longer than 28 years to gain.

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